Home > Travel Styles > Adventure Tours > Sailing Trips > October

Sailing Trips Starting In October 2027 and 2028

Are you looking to embark on a sailing trip in October 2027 or 2028? Choose from 33 unique trip itineraries and 806 departures from the world's leading touring operators.
Filter Results
33 Trips (806 Departures)
33 Trips (806 Departures)
Departures
Duration
7 Days
26 Days
Regions
Trip Styles
Show More...
Budget
Start & End Cities
Operators
Price
$1,100pp
$22,449pp
Countries
Show More...
8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise
 (1)

8 Days (7 Nights) Dubrovnik to Split
Operator: Intrepid
Departures: May 2027 to Oct 2028
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,740
Save 209
Per Person
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operator: G Adventures
Departures: Apr 2027 to Oct 2027
Visits: Croatia, Montenegro
Exclusive Savings
From (Per Person)
A$1,803
Save 826
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operator: Intrepid
Departures: Dec 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$4,003
Save 584
Per Person
View Trip
8 Day Sail & Hike Greece: Athens to Mykonos with Intrepid Travel
New ReleaseCruise

8 Days (7 Nights) Lavrio to Mykonos
Operator: Intrepid
Departures: Apr 2027 to Oct 2028
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,647
Save 204
Per Person
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok to Labuan Bajo
Operator: TruTravels
Departures: Apr 2027 to Nov 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$1,135
Save 899
Per Person
View Trip
8 Day Sail Greece: Santorini to Mykonos with Intrepid Travel
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operator: Intrepid
Departures: May 2027 to Sep 2028
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,559
Save 202
Per Person
View Trip
7 Day Amalfi Coast Sailing Adventure with Intrepid Travel
Cruise

7 Days (6 Nights) Naples to Procida
Operator: Intrepid
Departures: May 2027 to Sep 2028
Visits: Italy
Exclusive Savings
From (Per Person)
A$3,958
Save 233
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operator: G Adventures
Departures: Apr 2027 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,803
Save 826
Per Person
View Trip
14 Day Highlights of Sri Lanka with Maldive Dhoni Cruise (East Coast) with Explore Worldwide
Tour + Cruise

14 Days Negombo to Male
Operator: Explore
Departures: Aug 2027 to Oct 2027
Trip Styles: Adventure, Small Group, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$5,698
Save 439
Per Person
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Nov 2026 to Jan 2029
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,790
Save 1,033
Per Person
View Trip
8 Day Indonesia Sailing Adventure: Raja Ampat with Intrepid Travel
New ReleaseCruise

8 Days (7 Nights) Sorong to Sorong
Operator: Intrepid
Departures: Dec 2026 to Dec 2028
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$4,939
Save 258
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operator: G Adventures
Departures: May 2027 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,319
Save 326
Per Person
View Trip
8 Day Montenegro Sailing Adventure from Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operator: Intrepid
Departures: Jun 2027 to Oct 2028
Visits: Croatia, Montenegro
Exclusive Savings
From (Per Person)
A$2,838
Save 208
Per Person
View Trip
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operator: G Adventures
Departures: Jan 2027 to Dec 2027
Trip Styles: Adventure, Small Group, Sailing
Visits: India, Maldives
Exclusive Savings
From (Per Person)
A$3,623
Save 831
Per Person
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operator: TruTravels
Departures: Apr 2027 to Oct 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$3,373
Save 2,422
Per Person
View Trip
8 Day Maldive Dhoni Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Male to Male
Operator: Explore
Departures: Nov 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$3,212
Save 410
Per Person
View Trip
7 Day Sailing the Canary Islands with G Adventures
Cruise

7 Days (6 Nights) San Miguel de Abona to San Miguel de Abona
Operator: G Adventures
Departures: Nov 2026 to Apr 2028
Visits: Spain
Exclusive Savings
From (Per Person)
A$1,146
Save 803
Per Person
View Trip
10 Day Signature: Egypt's Cairo, Luxor & the Nile Valley with G Adventures
New ReleaseTour + River Cruise

10 Days Cairo to Cairo
Operator: G Adventures
Departures: Feb 2027 to Apr 2028
Rivers: Nile
Visits: Egypt
Exclusive Savings
From (Per Person)
A$11,759
Save 270
Per Person
View Trip
7 Day Egypt: Ancient Wonders & Temples of the Nile with G Adventures
New ReleaseTour

7 Days Cairo to Luxor
Operator: G Adventures
Departures: Dec 2026 to Jan 2028
Trip Styles: Adventure, Small Group, Sailing
Visits: Egypt
Exclusive Savings
From (Per Person)
A$4,056
Save 897
Per Person
View Trip
17 Day Signature: Egypt & Jordan's Ancient Wonders with G Adventures
New ReleaseTour + River Cruise

17 Days Cairo to Dead Sea
Operator: G Adventures
Departures: Feb 2027 to Apr 2028
Rivers: Nile
Visits: Egypt, Jordan
Exclusive Savings
From (Per Person)
A$19,893
Save 449
Per Person
View Trip
10 Day Egypt: Pyramids, Temples & the Nile with G Adventures
New ReleaseTour + River Cruise

10 Days Cairo to Cairo
Operator: G Adventures
Departures: Dec 2026 to Dec 2027
Rivers: Nile
Visits: Egypt
Exclusive Savings
From (Per Person)
A$6,482
Save 2,337
Per Person
View Trip
8 Day Sailing Greece - Santorini to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operator: G Adventures
Departures: May 2027 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,072
Save 311
Per Person
View Trip
8 Day Croatia Sailing Adventure: Split to Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operator: Intrepid
Departures: May 2027 to Oct 2028
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,740
Save 211
Per Person
View Trip
8 Day Sail Greece: Mykonos to Santorini with Intrepid Travel
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operator: Intrepid
Departures: May 2027 to Sep 2028
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,657
Save 204
Per Person
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Nov 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,057
Save 942
Per Person
View Trip
8 Day Sail & Hike Greece: Mykonos to Athens with Intrepid Travel
New ReleaseCruise

8 Days (7 Nights) Mykonos to Lavrio
Operator: Intrepid
Departures: Apr 2027 to Oct 2028
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,647
Save 204
Per Person
View Trip
7 Day Maldives Cruise: Indian Ocean Dhoni Life with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Dec 2026 to Jan 2028
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,114
Save 1,205
Per Person
View Trip
15 Day Croatia and Montenegro Sailing Adventure with Intrepid Travel
Cruise

15 Days (14 Nights) Split to Dubrovnik
Operator: Intrepid
Departures: Jun 2027 to Sep 2028
Visits: Croatia, Montenegro
Exclusive Savings
From (Per Person)
A$5,705
Save 270
Per Person
View Trip
14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operator: G Adventures
Departures: Dec 2026 to Dec 2028
Trip Styles: Adventure, Small Group, Island Hopping, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$4,497
Save 1,032
Per Person
View Trip
8 Day Sailing Greece - Mykonos to Athens with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Athens
Operator: G Adventures
Departures: Apr 2027 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,611
Save 738
Per Person
View Trip
Results: 1-30 of 33

No trips found. Try adjusting the search filters.




Trips found! Scroll up to view.

Adventure Travel

Walking and Hiking Everest Base Camp Treks Sailing Trips Ski Trips Cycling Tours Kayaking Tours Camping Tours Rafting Tours Wildlife Tours & Cruises Gorilla Treks

Trip Lengths

10 Day 2 Week 7 Day

Departure Months

November December January February March April May June July August September October
© 2010-2026. Global Journeys.
    

Global Journeys | Terms & Conditions

Global Journeys Pty Ltd. Accredited Member of The Australian Travel Industry Association (ATIA). No. A11351.

Travel Industry Associations